Preparation and characterization of Cu based on 5,5'-bistetrazole as a recyclable metal-organic framework and application in synthesis of diaryl ether by the Ullmann coupling reaction

Article abstract of DOI:10.1080/00958972.2021.1914333

Cu based on 5,5′-bistetrazole ([Cu₂BT · 2H₂O] _n) as a recyclable metal-organic framework (MOF) heterogeneous catalyst was characterized by FT-IR, ¹³C NMR, XRD, SEM, EDX, BET, BJH, and ICP-AES analysis. The catalytic activity of the catalyst was probed through the Ullmann reaction for synthesis of diaryl ether derivatives from two component reactions of aromatic arylhalides and phenol derivatives in DMSO. Simple procedure, high yields, short reaction time, and environmentally benign methods are advantages of this protocol. The catalyst was readily separated by simple filtration and reusable without significant loss of its catalytic efficiency.

Full text of DOI:10.1080/00958972.2021.1914333

Journal of Coordination Chemistry
ISSN: (Print) (Online) Journal homepage: https://www.tandfonline.com/loi/gcoo20
Preparation and characterization of Cu based on
5,5'-bistetrazole as a recyclable metal-organic
framework and application in synthesis of diaryl
ether by the Ullmann coupling reaction
Zeinab Noorpoor & Saeed Tavangar
To cite this article: Zeinab Noorpoor & Saeed Tavangar (2021) Preparation and characterization
of Cu based on 5,5'-bistetrazole as a recyclable metal-organic framework and application in
synthesis of diaryl ether by the Ullmann coupling reaction, Journal of Coordination Chemistry,
74:9-10, 1651-1662, DOI: 10.1080/00958972.2021.1914333
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JOURNAL OF COORDINATION CHEMISTRY
2021, VOL. 74, NOS. 9–10, 1651–1662
https://doi.org/10.1080/00958972.2021.1914333
Preparation and characterization of Cu based on 5,5’-
bistetrazole as a recyclable metal-organic framework
and application in synthesis of diaryl ether by the
Ullmann coupling reaction
Zeinab Noorpoor and Saeed Tavangar
Chemical Engineering, Malek-Ashtar University of Technology, Tehran, Iran
ABSTRACT
ARTICLE HISTORY
Cu based on 5,50-bistetrazole ([Cu2BT ꢀ 2H2O]n) as a recyclable
metal-organic framework (MOF) heterogeneous catalyst was char-
acterized by FT-IR, 13C NMR, XRD, SEM, EDX, BET, BJH, and ICP-
AES analysis. The catalytic activity of the catalyst was probed
through the Ullmann reaction for synthesis of diaryl ether deriva-
tives from two component reactions of aromatic arylhalides and
phenol derivatives in DMSO. Simple procedure, high yields, short
reaction time, and environmentally benign methods are advan-
tages of this protocol. The catalyst was readily separated by sim-
ple filtration and reusable without significant loss of its catalytic
efficiency.
Received 1 December 2020
Accepted 10 March 2021
KEYWORDS
Ullmann reaction; MOF;
catalyst; 5,50-
bistetrazole;
[Cu2BT ꢀ 2H2O]n
1. Introduction
Metal-organic framework (MOF) materials are porous crystalline solids with specific sur-
face areas surpassing activated nitrogen, carbons, and zeolites, composed of metal-
containing nodes connected by organic linkers through coordination bonds. They are
crystalline solids assembled with metal ions and organic ligands with a range of appli-
cations [1, 2]. Metal-organic frameworks (MOFs) have attracted attention in catalysis
CONTACT Saeed Tavangar
S_Tavangar@Yahoo.com
Chemical Engineering, Malek-Ashtar University of
Technology, Iran
ß 2021 Informa UK Limited, trading as Taylor & Francis Group

1652
Z. NOORPOOR AND S. TAVANGAR
because of their large specific surface areas and high porosities [3, 4]. The catalysts are
useful in organic transformations due to their high specific surface area, large and uni-
form porous networks, easy structural functionalization, and size-selectivity and shape-
selectivity [5]. Attainable and large open pores permit transport of guest reactants
into the frameworks to interact with active sites [6, 7]. Also, they are remarkably
robust and, hence well suited to catalysis under harsh conditions [8]. Diaryl ethers are
a significant category of organic compounds in life sciences industries like pharma-
ceuticals, polymers, and agricultural chemicals [9].
These compounds are synthesized by the Ullmann coupling reaction of phenols
with aryl halides (bromide or iodide) in the presence of stoichiometric or even greater
quantities of copper salts as catalyst at high temperatures under basic conditions [7,
10]. The Ullmann reaction or Ullmann coupling was first reported in 1901. It is a cou-
pling between aryl halides and copper that is named after Fritz Ullmann [11]. This
reaction has attracted high interest from industry and is used by chemists to produce
a C–C bond between two aromatic nuclei in the presence of copper powder as an
economical catalyst to prepare the corresponding symmetric biaryl.
Diaryl ethers and derivatives form an important class of organic compounds that
are key to polymer and life sciences industries in biologically active natural products.
The synthesis of natural cyclopeptides, such as vancomycin and anti-HIV agents like
chloropeptin, which contain this substructure, has captured substantial attention.
Traditional route to preparation of diaryl ethers is Pd-catalyzed or Cu-catalyzed
Ullmann coupling of aryl halides and phenols to form a C–O bond [12–14]. In spite of
the efficiency of Pd-catalyzed Ullmann coupling, the use of expensive palladium and
elaborate phosphorus ligands limit its use in industrial-scale production [10–14].
Many catalysts such as palladium [15, 16], ligand-free copper [17], and UiO-66-NH2
metal-organic frameworks [6] have been employed for synthesis of diaryl ethers via
Ullmann reaction. Catalysts based on MOFs serve as hosts for catalytic designs in vari-
ous different forms including without prior structural modification, with placing cata-
lyst on the surface or incorporation in the pores [18], and/or structural post
modification [19]. In fact, eco-friendly heterogeneous copper-based catalysts for the
Ullmann reactions should be developed due to easy handling, simplicity in workup,
recoverability and reusability [4]. Different MOFs due to high surface area and porosity
as solid heterogeneous catalysts have received enormous attention [20–25]. Reports of
modified MOFs based on copper have been reported [26, 27].
In continuation of our research [28–30], we present results on the preparation and
characterization of a metal-organic framework (MOF) with Cu and 5,50-bistetrazole
([Cu2BT ꢀ 2H2O]n) and its catalytic application for preparation of diaryl ether derivatives
using Ullmann coupling via O-arylation reactions from aryl halide (1 mmol), phenol
derivative (1 mmol), and 0.1 g of K2CO3 in DMSO (7 mL) (Scheme 1).
2. Experimental
2.1. Chemicals and apparatus
The X-ray powder diffraction (XRD) of the desired catalyst was carried out on a Philips
PW 1830 X-ray diffractometer with CuKa source (k ¼ 1.5418 Å) for Bragg’s angle

JOURNAL OF COORDINATION CHEMISTRY
1653
Scheme 1. Ullmann coupling reaction with [Cu2BT ꢀ 2H2O]n as a recyclable metal-organic frame-
work catalyst.
(10–80ꢁ) at 25 ꢁC. Fourier transform infrared (FT-IR) spectrum was obtained using a FT-
IR spectrometer (Vector 22-Bruker) from 400 to 4000 cmꢂ1 at room temperature.
Scanning electron microscopy (SEM) analysis was recorded using a VEGA//TESCAN
KYKY-EM 3200 microscope (acceleration voltage 26 kV). The elemental analysis was
examined by energy dispersive X-ray (EDX), VEGA3 XUM/TESCAN. NMR spectra were
1
recorded with a Bruker DRX-400 AVANCE instrument (300.1 MHz for H, 75.4 MHz for
13C). The spectra were evaluated in DMSO-d6 as solvent. The metal loading was dis-
cerned by an inductively coupled plasma-atomic emission spectrometer (ICP-AES).
Melting points were estimated on an Electrothermal 9100 apparatus.
2.2. General procedure
2.2.1. Preparation of 5,50-bistetrazole (H2BT)
In a 1 L flask, it dissolved 1 mol of sodium cyanide and 1 mol of sodium azide in
300 mL of distilled water in an ice bath by mechanical stirring. After the reactants
were completely dissolved, 0.64 mol of magnesium dioxide was added and stirred for
1 h with a mechanical stirrer. Then, in a 500 mL flask, 54 mL sulfuric acid (96%), 76 mL
of glacial acetic acid, 0.013 mol of 5% copper sulfate, and 100 mL of distilled water
were prepared and the reaction mixture was stirred in the ice bath for 1 h. After that,
the resulting solution was added dropwise to the first solution. After 1 h, the obtained
mixture was refluxed at 60 ꢁC for 15 h. Then the reaction mixture was stirred at 85 ꢁC
for 15 h and filtered giving a gray solid product (bistetrazole).
Next, in a 1 L beaker, 0.66 mol of sodium carbonate was dissolved in 200 mL of
water, then the bistetrazole salt was added and heated at 80 ꢁC for 30 min. The solu-
tion was filtered to separate the obtained blue solution which was added to 200 mL
of 37% HCl and heated to dissolve the precipitate completely with solution yellow.
Then, the reaction vessel was cooled overnight giving crystals. To further purify the
product, the obtained solid was recrystallized by boiling water again which led to the
H2BT product.

1654
Z. NOORPOOR AND S. TAVANGAR
Table 1. Computational values from EDX analysis of [Cu2BT ꢀ 2H2O]n.
% C
8.04
%O
%N
%Cu
%H
1
10.32
37.27
43.01
1.36
2.2.2. Spectra of 5,5’-bistetrazole (H2BT)
White powder, m.p.: 254–255 ꢁC; IR (KBr): ꢀmax ¼ 3177, 3014, 2803, 2692, 2657, 2513,
1
1626, 1529, 1500, 685 cmꢂ1; H NMR (400.13 MHz, DMSO): d ¼ 9.27 (s, 2H, CH) ppm;
13C NMR (100.6 MHz, DMSO): d ¼ 148 (C–H) ppm.
2.2.3. Preparation of the metal-organic framework [Cu2BT ꢀ 2H2O]n
To prepare [Cu2BT ꢀ 2H2O]n by co-precipitation, first, in a 100 mL flask, 1.16 mmol H2BT
ligand and 0.2 mmol Cu(NO3)2 ꢀ 3H2O were dissolved in 15 mL distilled water and
refluxed for 3 h. After cooling, the product was separated by filtration and washed sev-
eral times with distilled water to remove impurities and unreacted materials and
[Cu2BT ꢀ 2H2O]n was obtained.
2.2.4. General procedure for synthesis of diaryl ethers via Ullmann coupling using
[Cu2BT ꢀ 2H2O]n as the catalyst
To prepare diaryl ethers using Ullmann coupling reaction via O-arylation reactions
from aryl halide (1 mmol), phenol derivative (1 mmol), and 0.1 g of K2CO3 in DMSO
(7 mL) were placed into a round bottom flask containing [Cu2BT ꢀ 2H2O]n (5 mg). The
obtained mixture was refluxed at 70 ꢁC for 1 h under robust stirring. The reaction mix-
ture was cooled after completion of the reaction and the catalyst was separated by fil-
tration. The filtrate was vaporized on a rotary evaporator and the crude product was
purified by column chromatography using ethyl acetate/n-hexane.
2.2.5. Selected spectra for two products are given below
3-Nitrophenyl-2,6-dimethoxyphenyl ether (Table 2, entry 9). m.p.: 35–36 ꢁC; 1H NMR
(400.13 MHz, DMSO): d ¼ 4.10 (s, 6H, OCH3), 6.52–6.64 (m, 3H), 7.09–7.15 (m, 2H),
7.33–7.38 (m, 2H) ppm; 13C NMR (100.6 MHz, DMSO): d ¼ 51.8, 117.0, 117.2, 118.1, 121.5,
124.2, 128.2, 129.1, 132.0, 131.0, 135.2 ppm.
3-Nitrophenyl-2,6-dimethylphenyl ether (Table 2, entry 12). m.p.: 42 ꢁC; 1H NMR
(400.13 MHz, DMSO): d ¼ 2.10 (s, 6H, CH3), 7.05–7.13 (m, 3H), 7.20–7.25 (m, 3H), 7.38 (s,
1H) ppm; 13C NMR (100.6 MHz, DMSO): d ¼ 22.0, 121.9, 121.9, 124.0, 128.0, 128.5, 128.9,
129.3, 130.1, 130.9, 134.3 ppm.
3. Results and discussion
3.1. Characterization of [Cu2BT ꢀ 2H2O]n
3.1.1. Fourier Transform Infrared (FT-IR) Analysis of H2BT and [Cu2BT ꢀ 2H2O]n
FT-IR spectra of H2BT and [Cu2BT ꢀ 2H2O]n are shown in Figure 1. The NH-related peak
at 3177 cmꢂ1 as well as the peak related to the tetrazole rings at 3014, 2803, 2692,
2657, and 2513 cmꢂ1 are shown. The peaks at 1626 and 1529 cmꢂ1 belong to the
C ¼ N group, and peaks at 1500 to 685 cmꢂ1 are the bending and stretching vibrations

JOURNAL OF COORDINATION CHEMISTRY
1655
Table 2. Optimization conditions for preparation of diphenyl ether in the presence of
[Cu2BT ꢀ 2H2O]n as a recyclable metal-organic framework.
Amount of
catalyst (mg)
Entry
Solvent
Temperature (ꢁC)
Time (h)
Yield (%)a
1
2
3
4
10
10
10
10
CH3OH
DMSO
H2O
CH3CN
DMF
70
100
100
70
7
5
8
8
8
63
90
47
59
75
5
10
110
6
7
8
9
10
11
12
13
14
10
2
5
10
2
5
10
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
25
50
50
50
70
70
70
70
10
5
5
5
2
1
1
24
24
Trace
25
50
62
80
95
96
Trace
–
H2BT
Catalyst free
70
aYields refer to isolated product.
Figure 1. FT-IR spectra of H2BT and [Cu2BT ꢀ 2H2O]n.

1656
Z. NOORPOOR AND S. TAVANGAR
Figure 2. XRD analysis corresponding to the synthetic framework of [Cu2BT ꢀ 2H2O]n.
of the C–C, C ¼ N, and N–H groups. [Cu2BT ꢀ 2H2O]n shows peaks related to the
tetrazole rings at 3582 and 3526 cmꢂ1. Peaks at 1622 cmꢂ1 belong to the C ¼ N
group, and other peaks at 1100 to 518 cmꢂ1 correspond to the symmetric, asym-
metric, and bending vibrations of the C–C and C ¼ N groups. According to the
spectra, formation of [Cu2BT ꢀ 2H2O]n is confirmed (Figure 1). In the FT-IR spectrum
of [Cu2BT ꢀ 2H2O]n, the intensity of the adsorption bands for the bending vibration
of C–H, N–H, and C ¼ N in 5,50-bistetrazole heterocyclic ring is reduced after forma-
tion of the complex with Cu. Therefore, the obtained data from FT-IR spectroscopy
prove the existence of the H2BT and Cu in the structure of [Cu2BT ꢀ 2H2O]n MOF
(figure 1).
3.1.2. X-ray diffraction (XRD) analysis
Figure 2 shows the XRD spectrum of [Cu2BT ꢀ 2H2O]n. XRD measurements were per-
formed to confirm the presence of Cu and 5,50-bistetrazole. Broad peaks related to
Cu(II) appeared at 2h ¼ 42, 50, and 72, confirming the presence of metal in the struc-
ture. The average [Cu2BT ꢀ 2H2O]n was calculated to be about 2 nm from the XRD
results by Scherrer’s equation, D ¼ k k/b cosө, where k is a constant (generally consid-
ered as 0.94), k is the wavelength of Cu Ka (1.54 ˚A), b is the corrected diffraction line
full-width at half-maximum (FWHM), and ө is Bragg’s angle (Figure 2).
3.1.3. EDX analysis of [Cu2BT ꢀ 2H2O]n MOF
The results of Energy Dispersive X-Ray Analysis (EDX) for [Cu2BT ꢀ 2H2O]n are shown in
Table 1. The results indicated 37.27% N, 8.04% C, 1.36% H, 10.32% O, and 43.01% Cu
in the catalyst.
3.1.4. ICP-AES elemental analysis
The ICP-AES analysis is performed to determine the amount of Cu (82,520 mg kgꢂ1) in
CNC-AMPD-Pd as catalyst. The inductively coupled plasma-atomic emission spectros-
copy (ICP-AES) analysis showed the weight percentage of Pd to be 43% wt.

JOURNAL OF COORDINATION CHEMISTRY
1657
Figure 3. Scanning electron microscopy (SEM) of [Cu2BT ꢀ 2H2O]n: (a) (2 lm); (b) (500 nm);
(c) (200 nm).
Figure 4. Nitrogen adsorption-desorption isotherm (BET method) of [Cu2BT ꢀ 2H2O]n.
To have an estimation of Cu content in the catalyst, the ICP-AES analysis was car-
ried out. The ICP-AES analysis showed the weight percentage of Cu to be 43% wt in
[Cu2BT ꢀ 2H2O]n metal-organic frameworks.
3.1.5. Scanning electron microscopy (SEM) of [Cu2BT ꢀ 2H2O]n
In Figure 3, the morphology of [Cu2BT ꢀ 2H2O]n by co-precipitation method is illus-
trated in different sizes, 2 lm, 500 nm, and 200 nm. As shown in Figure 3, the mor-
phologies of [Cu2BT ꢀ 2H2O]n are made up of interconnected granular particles nearly
200 nm size in diameter.
3.1.6. Nitrogen adsorption-desorption isotherm (BET and BJH method)
of [Cu2BT ꢀ 2H2O]n
The nitrogen desorption-adsorption isotherm curve of [Cu2BT ꢀ 2H2O]n is shown in
Figure 4. According to this analysis, the effective surface area is 28.519 m2 gꢂ1 and the
total volume of pores is 0.1997 cm3 gꢂ1. BJH calculations show that the pore size of
[Cu2BT ꢀ 2H2O]n is 6.91 nm (Figure 5).

1658
Z. NOORPOOR AND S. TAVANGAR
Figure 5. BJH of [Cu2BT ꢀ 2H2O]n.
3.1.7. Catalytic application of [Cu2BT ꢀ 2H2O]n
To find optimum conditions, the reaction of iodobenzene and phenol for the synthe-
sis of diphenyl ether in the presence of the catalyst was performed. The reaction
was carried out with different amounts of [Cu2BT ꢀ 2H2O]n (2, 5, and 10 mg) as cata-
lyst in 7 mL DMSO at different temperatures. As can be seen in Table 2, the opti-
mum reaction conditions are [Cu2BT ꢀ 2H2O]n (5 mg) in 7 mL DMSO at 70 ꢁC (Table 2,
entry 11).
To investigate the scope and limitations of [Cu2BT ꢀ 2H2O]n as catalyst a variety of
phenols were reacted with various substituted phenyl halides under the optimum
reaction conditions and the results are reported in Table 3. Starting materials, either
with electron-donating or electron-withdrawing substituents, provided the desired
products in high to excellent yields (Table 3).
To compare the present work with reported results, a summary of the results for
preparation of diphenyl ether is presented in Table 4. The results show that
[Cu2BT ꢀ 2H2O]n as catalyst was performed in short times and similar yields with simple
workup procedure which makes it an applicable method for preparation of these com-
pounds in comparison with the reported results (Table 4).
Additionally, the recycling and reusability of [Cu2BT ꢀ 2H2O]n as catalyst was studied
using the model reaction (section 2). After completion of the reaction, the reaction
mixture was cooled and the catalyst was separated by filtration, washed with deion-
ized water and ethanol, and dried for the next experiment. According to the observed
results, the recovered catalyst was reused six runs without any loss of its activity
(Figure 6). The XRD and SEM analysis of recycled [Cu2BT ꢀ 2H2O]n (after six times recy-
cling) was provided and is shown in Figures 7 and 8. As can be seen, the structure of
the recycled nanocatalyst has not changed.

JOURNAL OF COORDINATION CHEMISTRY
1659
Table 3. Synthesis of diaryl ethers in the presence of [Cu2BT ꢀ 2H2O]n as a recyclable metal-
organic framework catalyst.
Melting point (ꢁC)
Entry
1
Aryl halide
Phenols
OH
Yield (%)
95
TON
57
TOF (1/h)
57
Found
32
Reported [31–34]
I
31
OH
Me
I
I
2
3
93
93
56
56
56
56
21–22
61–62
21.5 ꢂ 22
OH
61.9 ꢂ 62.2
Me
NO2
OH
I
4
5
6
7
95
92
92
92
57
55
55
55
57
55
55
55
21–22
48–49
32
20
Me
I
OH
47 ꢂ 49
31
NO2
Br
OH
OH
Br
56–57
56 ꢂ 58
NO2
OH
Me
Br
8
93
56
56
23
21.5 ꢂ 22
Br
OH
OH
9
90
93
54
56
54
56
35–36
35–37
H3CO
OCH3
NO2
Br
10
63
63 ꢂ 64
NO2
Cl
Br
OH
11
12
95
89
57
53
57
53
46-47
42
46
NO2
Cl
OH
Br
41–42
NO2
(continued)

1660
Z. NOORPOOR AND S. TAVANGAR
Table 3. Continued.
Melting point (ꢁC)
Found Reported [31–34]
Entry
13
Aryl halide
Cl
Phenols
Yield (%)
92
TON
55
TOF (1/h)
55
OH
64
63 ꢂ 64
NO2
Br
OH
Cl
14
95
57
57
63
61.9 ꢂ 62.2
Me
NO2
Cl
OH
OH
15
16
92
92
55
55
55
55
31–32
31
Cl
57
56 ꢂ 58
NO2
TON: (turnover number, yield of product/mol of MOF). TOF: (turn over frequency, TON/time of reaction).
Table 4. Comparison of the results of [Cu2BT ꢀ 2H2O]n with other catalysts in the ullman reaction
for synthesis of diphenyl ether.
Entry
Catalyst
Conditions
Time
Yield (%)a [Ref]
1
2
3
4
5
MWCNTs-Met/CuCl (20 mg)
K2CO3, DMF, 80 ꢁC
K2CO3, DMF, 110 ꢁC
K2CO3, DMF, 100 ꢁC
DMSO, K2CO3, 120 ꢁC
K2CO3, DMSO, 70 ꢁC
8 h
12 h
24 h
15 h
1 h
96 [31]
90 [32]
96 [33]
95 [34]
95
Fe3O4@mPANI (2 mg), Cu2O (5 mol%)
GO-CPTMS@HPTPy-Pd-TPy (1.38 mmol)
Fe3O4/CS-Cu NPs (20 mg)
[Cu2BT ꢀ 2H2O]n (5 mg)
[Present work]
aYields refer to isolated pure products.
Figure 6. The recycling of [Cu2BT ꢀ 2H2O]n as catalyst.

JOURNAL OF COORDINATION CHEMISTRY
1661
Figure 7. XRD analysis of [Cu2BT ꢀ 2H2O]n nanoparticles after six times recycling.
Figure 8. SEM of [Cu2BT ꢀ 2H2O]n nanoparticles after six times recycling.
4. Conclusion
We report the preparation of
a
Cu compound based on 5,50-bistetrazole
([Cu2BT ꢀ 2H2O]n) as an efficient and reusable heterogeneous MOF catalyst. The pre-
pared [Cu2BT ꢀ 2H2O]n as a MOF catalyst was characterized by FT-IR, XRD, SEM, EDX,
BET, BJH, and ICP-AES analysis techniques and used for the Ullmann coupling reaction
via O-arylation reactions from aryl halides with phenol derivatives. The prepared MOF
exhibited several advantages, including good porosity for more availability, simple pro-
cedure, easy separation, biocompatibility, high yields of obtained products and good
reversibility.
Funding
This research was supported by the Research Council of the Malek-Ashtar University of
Technology in Iran.

1662
Z. NOORPOOR AND S. TAVANGAR
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